(+)-(S)-2-(5-bromopyridin-2-yloxy)-2-phenylacetic acid | 1196831-42-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(S)-2-(5-bromopyridin-2-yloxy)-2-phenylacetic acid
• CAS: 1196831-42-1
• 化学式: C₁₃H₁₀BrNO₃
• 分子量: 308.131
• InChiKey: ICIQHUAJYIKTIM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  18.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  59.42
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  5-溴-2-碘吡啶 、 (S)-(+)-扁桃酸 在 copper(l) iodide 、 caesium carbonate 作用下， 以 丁腈 为溶剂， 反应 15.0h， 以16%的产率得到(+)-(S)-2-(5-bromopyridin-2-yloxy)-2-phenylacetic acid
  参考文献：
  名称：

  One-step synthesis of homochiral O-aryl and O-heteroaryl mandelic acids and their use as efficient 1H NMR chiral solvating agents

  摘要：

  Job and Buchwald's one-step copper-promoted arylation of hydroxyl groups was explored and modified so that it could be applied to the coupling of mandelic acid with several halobenzenes and haloheteroarenes. A number of new homochiral O-aryl and O-heteroaryl mandelic acids, generally presenting high enantiomeric purities, were obtained. Although yields were moderate at the best, ranging from 9% to 41%, the reaction was convenient enough to prepare new mandelic acid derivatives, some of which performed as efficient chiral solvating agents (CSAs) for the direct H-1 NMR ee value determination of several clinically and pharmacologically relevant amines. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.08.002